2002 Porsche 911 Turbo - 19k miles - $53,500 - Chicago, IL

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Fifty grand is hardly a bargain for any car, but for this 996 with not even 20k miles, it does represent the cheapest way behind the wheel of a mint condition 911 Turbo. That’s because the 996, as the first water-cooled 911, is the least-loved generation of Porsche’s iconic model, and because this particular car is fitted with the least-loved Porsche transmission, the Tiptronic, which is basically an old school slushbox automatic.

But if you can ignore the hateful stares of Porsche purists, I think you’ll find that there’s something quite satisfying about piloting a 415 hp supercar with a surprisingly capable (especially for the day) automatic.

For one thing, the torque converter helps to quell turbo lag and keep the motor on boost – which means you can stop worrying about your heel-and-toe technique and instead simply focus on steering the damn thing around the next bend, which at the speeds it’s capable of is going to be coming at you fast.

Then, when you just need to get to an appointment in heavy traffic, it’s equally capable of that too.

And Car and Driver didn’t exactly hate it when they reviewed the model in 2001:

So if you prefer your Porsche with a bit less of an edge – but still 99% of the performance – this would be a very good choice.

Offered on craigslist HERE by a private seller in the Chicago area for $53,500, which is a reasonable price for such an exceptionally nice 911 Turbo, even one with an automatic.

VIN: WP0AB299X2S687197

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Probably my favorite Porsche. Such a tech-heavy machine for its time. I remember reading every single word that was penned about this car when it came out.

To me, this represents the best era of cars. Technologically advanced without being too much, plus design-wise I love the body scoops and intakes of the turbo model. I’m a big fan of all those gaudy race car style cues, and back then they were actually cool. You know, before Camrys came with scoops and intakes…

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Agreed. The 996 gets knocked for its looks, but I think the 996 Turbo is one of the best looking 911s ever.